Skip to Content
Merck
All Photos(3)

Documents

R2408

Sigma-Aldrich

Rosiglitazone

≥98% (HPLC), powder, PPARγ agonist

Sign Into View Organizational & Contract Pricing

Synonym(s):
Rosiglitazone, 5-[[4-[2-(Methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione
Linear Formula:
C18H19N3O3S
CAS Number:
Molecular Weight:
357.43
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

powder

solubility

DMSO: ≥10 mg/mL

originator

GlaxoSmithKline

storage temp.

2-8°C

SMILES string

CN(CCOc1ccc(CC2SC(=O)NC2=O)cc1)c3ccccn3

InChI

1S/C18H19N3O3S/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15/h2-9,15H,10-12H2,1H3,(H,20,22,23)

InChI key

YASAKCUCGLMORW-UHFFFAOYSA-N

Gene Information

human ... PPARG(5468)

Looking for similar products? Visit Product Comparison Guide

General description

Rosiglitazone is a member of the thiazolidinedione family. It effectively lowers glucose levels by enhancing the response of target cells to insulin, without causing increased stimulation and release of insulin by the pancreatic beta cells. Rosiglitazone functions by activating the nuclear peroxisome proliferator-activated (PPAR) receptor gamma, which plays a key role in regulating adipogenesis, glucose metabolism, and genetic networks. It exhibits high potency as a thiazolidinedione, with a binding affinity for PPAR-gamma that is 30-fold higher than pioglitazone. Furthermore, it increases insulin-stimulated IRS-1/2 in skeletal muscle and adipose tissue, leading to the expression of the GLUT4 glucose transporter.

Application

Rosiglitazone has been used:
  • as a medium constituent for adipocyte differentiation
  • in the cell proliferation assay in human colonic carcinoma cell lines
  • for Bcl-2-like protein 13 (Bcl2l13) expression in adipocytes
  • as a peroxisome proliferator-activated receptor gamma (PPARγ) ligand

Biochem/physiol Actions

Rosiglitazone is a potent agonist for PPARγ with an EC50 of 43 nM for the human receptor. It is antidiabetic, working as an insulin sensitizer by binding to the PPARγ receptors in fat cells and making the cells more responsive to insulin.

Features and Benefits

This compound is a featured product for ADME Tox and Gene Regulation research. Discover more featured ADME Tox and Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the AMPKs and Nuclear Receptors (PPARs) pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 1

1 of 1

Troglitazone A α-tocopherol (vitamin E) moiety containing thiazolidinedione class of insulin-sensitizer that acts as an activator of peroxisome proliferator-activated receptors γ (PPARγ).

Millipore

648469-M

Troglitazone

Siyu Xie et al.
Nutrients, 11(7) (2019-07-22)
Promoting white-to-beige adipocyte transition is a promising approach for obesity treatment. Although Liensinine (Lie), a kind of isoquinoline alkaloid, has been reported to affect white-to-beige adipocyte transition, its effects on inhibiting beige adipocytes recovering to white adipocytes and maintaining the
A novel role for Bcl2l13 in promoting beige adipocyte biogenesis
Ju L, et al.
Biochemical and Biophysical Research Communications, 506(3), 485-491 (2018)
Rosiglitazone
Rodriguez BSQ and Correa R
StatPearls [Internet] (2023)
Rosiglitazone diminishes the high-glucose-induced modulation of 5-fluorouracil cytotoxicity in colorectal cancer cells
Lau MF, et al.
EXCLI Journal , 17, 186-186 (2018)
María Isabel Cuartero et al.
Stroke, 44(12), 3498-3508 (2013-10-19)
Neutrophils have been traditionally recognized as major mediators of a deleterious inflammatory response in acute ischemic stroke, but their potential as a therapeutic target remains unexplored. Recent evidence indicates that neutrophils may acquire different phenotypes and contribute to resolution of

Articles

We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

Related Content

Discover Bioactive Small Molecules for Kinase Phosphatase Biology

Discover Bioactive Small Molecules for ADME/Tox

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service